Milwaukee (MKE) to Chicago (ORD), Dec 30, 2026: round trips from $306, one way from $178

Milwaukee (MKE) to Chicago (ORD), Dec 30, 2026: round trips from $306, one way from $178 on Axel, checked Oct 29, 2026. Lowest published fares: $306 round trip, Axel-exclusive, American Airlines, nonstop, Dec 30, 2026 – Jan 4, 2027; $178 one way, Axel-exclusive, American Airlines, nonstop, Dec 30, 2026; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Dec 30–31, 2026 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $107 total · 4★ Freehand Chicago, $83 total · 5★ Sofitel Chicago Magnificent Mile, $206 total
• Hotels in Chicago for these nights (Dec 30 – Jan 1, 2027 · 2 nights · 2 adults, 1 room): 3★ The Willows Hotel, $279 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $250 total · 5★ Sofitel Chicago Magnificent Mile, $667 total
• Hotels in Chicago for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $419 total · 4★ Freehand Chicago, $335 total · 5★ Sofitel Chicago Magnificent Mile, $873 total
• Hotels in Chicago for these nights (Dec 30 – Jan 3, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $535 total · 4★ Freehand Chicago, $415 total · 5★ Sofitel Chicago Magnificent Mile, $1,080 total
• Hotels in Chicago for these nights (Dec 30 – Jan 4, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $608 total · 4★ Freehand Chicago, $487 total · 5★ Sofitel Chicago Magnificent Mile, $1,338 total
• Hotels in Chicago for these nights (Dec 30 – Jan 5, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $681 total · 4★ Freehand Chicago, $558 total · 5★ Sofitel Chicago Magnificent Mile, $1,545 total
• Hotels in Chicago for these nights (Dec 30 – Jan 6, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $754 total · 4★ Freehand Chicago, $631 total · 5★ Sofitel Chicago Magnificent Mile, $1,744 total
• Hotels in Chicago for these nights (Dec 30 – Jan 7, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $835 total · 4★ Freehand Chicago, $704 total · 5★ Sofitel Chicago Magnificent Mile, $1,971 total
• Hotels in Chicago for these nights (Dec 30 – Jan 8, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $908 total · 4★ Freehand Chicago, $776 total · 5★ Sofitel Chicago Magnificent Mile, $2,235 total
• Hotels in Chicago for these nights (Dec 30 – Jan 9, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $993 total · 4★ Freehand Chicago, $856 total · 5★ Sofitel Chicago Magnificent Mile, $2,493 total
• Hotels in Chicago for these nights (Dec 30 – Jan 10, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,066 total · 4★ Freehand Chicago, $936 total · 5★ Sofitel Chicago Magnificent Mile, $2,695 total
• Hotels in Chicago for these nights (Dec 30 – Jan 11, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,139 total · 4★ Freehand Chicago, $1,006 total · 5★ Sofitel Chicago Magnificent Mile, $2,914 total
• Hotels in Chicago for these nights (Dec 30 – Jan 12, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,224 total · 4★ Freehand Chicago, $1,078 total · 5★ Sofitel Chicago Magnificent Mile, $3,120 total
• Hotels in Chicago for these nights (Dec 30 – Jan 13, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,297 total · 4★ Freehand Chicago, $1,149 total · 5★ Sofitel Chicago Magnificent Mile, $3,330 total

All hotels in Chicago

Route overview: Milwaukee to Chicago (ORD) flight deals

2026-12-30 · one way · Axel-exclusive $178.25

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.

2026-12-30 · one way · Axel-exclusive $184.00

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.

2026-12-30 → 2026-12-31 · Axel-exclusive $327.76

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA5004: ORD 2026-12-31 21:30:00 → MKE 2026-12-31 22:37:00; nonstop; 67 minutes. Local airport times.

2026-12-30 → 2026-12-31 · Axel-exclusive $339.26

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5822: ORD 2026-12-31 07:30:00 → MKE 2026-12-31 08:36:00; nonstop; 66 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $327.76

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4920: ORD 2027-01-01 13:14:00 → MKE 2027-01-01 14:21:00; nonstop; 67 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $339.26

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5362: ORD 2027-01-01 22:00:00 → MKE 2027-01-01 22:55:00; nonstop; 55 minutes. Local airport times.

2026-12-30 → 2027-01-02 · Axel-exclusive $327.76

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4963: ORD 2027-01-02 21:15:00 → MKE 2027-01-02 22:22:00; nonstop; 67 minutes. Local airport times.

2026-12-30 → 2027-01-02 · Axel-exclusive $339.26

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5758: ORD 2027-01-02 16:40:00 → MKE 2027-01-02 17:51:00; nonstop; 71 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $327.76

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4920: ORD 2027-01-03 12:30:00 → MKE 2027-01-03 13:37:00; nonstop; 67 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $339.26

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5933: ORD 2027-01-03 12:45:00 → MKE 2027-01-03 13:56:00; nonstop; 71 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4920: ORD 2027-01-05 12:30:00 → MKE 2027-01-05 13:37:00; nonstop; 67 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA4711: ORD 2027-01-05 19:48:00 → MKE 2027-01-05 20:59:00; nonstop; 71 minutes. Local airport times.

2026-12-30 → 2027-01-06 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4941: ORD 2027-01-06 18:16:00 → MKE 2027-01-06 19:32:00; nonstop; 76 minutes. Local airport times.

2026-12-30 → 2027-01-06 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5933: ORD 2027-01-06 12:45:00 → MKE 2027-01-06 13:56:00; nonstop; 71 minutes. Local airport times.

2026-12-30 → 2027-01-07 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA5004: ORD 2027-01-07 21:30:00 → MKE 2027-01-07 22:37:00; nonstop; 67 minutes. Local airport times.

2026-12-30 → 2027-01-07 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5822: ORD 2027-01-07 07:30:00 → MKE 2027-01-07 08:36:00; nonstop; 66 minutes. Local airport times.

2026-12-30 → 2027-01-09 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA3999: ORD 2027-01-09 14:00:00 → MKE 2027-01-09 15:04:00; nonstop; 64 minutes. Local airport times.

2026-12-30 → 2027-01-09 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5637: ORD 2027-01-09 15:35:00 → MKE 2027-01-09 16:46:00; nonstop; 71 minutes. Local airport times.

2026-12-30 → 2027-01-10 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4941: ORD 2027-01-10 18:16:00 → MKE 2027-01-10 19:32:00; nonstop; 76 minutes. Local airport times.

2026-12-30 → 2027-01-10 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5234: ORD 2027-01-10 10:50:00 → MKE 2027-01-10 12:05:00; nonstop; 75 minutes. Local airport times.

2026-12-30 → 2027-01-11 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4919: ORD 2027-01-11 08:29:00 → MKE 2027-01-11 09:38:00; nonstop; 69 minutes. Local airport times.

2026-12-30 → 2027-01-11 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5637: ORD 2027-01-11 15:35:00 → MKE 2027-01-11 16:46:00; nonstop; 71 minutes. Local airport times.

2026-12-30 → 2027-01-13 · Axel-exclusive $306.38

• American Airlines AA5014: MKE 2026-12-30 05:00:00 → ORD 2026-12-30 06:26:00; nonstop; 86 minutes. Local airport times.
• American Airlines AA4941: ORD 2027-01-13 18:16:00 → MKE 2027-01-13 19:32:00; nonstop; 76 minutes. Local airport times.

2026-12-30 → 2027-01-13 · Axel-exclusive $317.13

• United Airlines UA5412: MKE 2026-12-30 07:45:00 → ORD 2026-12-30 09:05:00; nonstop; 80 minutes. Local airport times.
• United Airlines UA5637: ORD 2027-01-13 15:35:00 → MKE 2027-01-13 16:46:00; nonstop; 71 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Milwaukee (MKE) to Chicago (ORD) · Dec 30, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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